The present invention relates to a process for preparing at least one ethylenically unsaturated, urethane group-containing compound from i) diisocyanate, ii) at least one compound having at least one hydroxyl group and at least one ethylenically unsaturated, polymerizable group, iii) and optionally at least one hydroxyl group-containing compound, in which 1 diisocyanate is subjected to a determination of the peroxide content immediately prior to the reaction, 2 a) if the determined peroxide content is greater than or equal to 20 mmol/kg, the diisocyanate is subjected to distillative purification until the determined peroxide content is less than 20 mmol/kg, or or b) if the determined peroxide content is less than 20 mmol/kg, no distillative purification is performed, and 3. then i) distilled diisocyanate of a) and/or untreated diisocyanate of b) is reacted with ii) at least one compound having at least one hydroxyl group and at least one ethylenically unsaturated, polymerizable group and optionally iii) with at least one hydroxyl group-containing compound to give an ethylenically unsaturated, urethane group-containing compound.

The present invention is directed to a compound of formula I, ##STR00001##
wherein R.sub.1 comprises hydrogen, an alkyl group, or an aryl group; R.sub.2 comprises hydrogen or a methyl group; R.sub.3 comprises a divalent organic group; R.sub.4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R.sub.5), wherein R.sub.5 comprises a monovalent organic group. The present invention is also directed towards polymers comprising a pendant carbamate-functional moiety comprising the structure: ##STR00002##
wherein R.sub.1 comprises hydrogen, an alkyl group, or an aryl group; R.sub.2 comprises hydrogen or a methyl group; R.sub.3 comprises a divalent organic group; R.sub.4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R.sub.5) wherein R.sub.5 comprises a monovalent organic group. The present invention is also directed to methods of preparing such compounds and polymers, compositions comprising such polymers, and coatings produced from such compositions.

The present invention is directed to a compound of formula I, ##STR00001##
wherein R.sub.1 comprises hydrogen, an alkyl group, or an aryl group; R.sub.2 comprises hydrogen or a methyl group; R.sub.3 comprises a divalent organic group; R.sub.4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R.sub.5), wherein R.sub.5 comprises a monovalent organic group. The present invention is also directed towards polymers comprising a pendant carbamate-functional moiety comprising the structure: ##STR00002##
wherein R.sub.1 comprises hydrogen, an alkyl group, or an aryl group; R.sub.2 comprises hydrogen or a methyl group; R.sub.3 comprises a divalent organic group; R.sub.4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R.sub.5) wherein R.sub.5 comprises a monovalent organic group. The present invention is also directed to methods of preparing such compounds and polymers, compositions comprising such polymers, and coatings produced from such compositions.

Compounds useful for formulating inks, 3D printing resins, molding resins, coatings, sealants and adhesives which exhibit reduced shrinkage stress and high hardness and stiffness when cured are described which include a single free radical-polymerizable functional group, one or more urethane and/or ureido linkages and one or more cyclic structural elements per molecule.

Compounds useful for formulating inks, 3D printing resins, molding resins, coatings, sealants and adhesives which exhibit reduced shrinkage stress and high hardness and stiffness when cured are described which include a single free radical-polymerizable functional group, one or more urethane and/or ureido linkages and one or more cyclic structural elements per molecule.

The present invention relates to urethane, thiourethane and urea adducts of tertiary amines and the use thereof as catalysts for the crosslinking of aliphatically, cycloaliphatically, araliphatically or aromatically bonded isocyanate groups with one another. The catalysts according to the invention have the particular advantage that they are thermolatent.

A composition is provided including a compound (A) represented by Formula (1) and a compound (B) represented by Formula (2), wherein the compound (B) is contained in an amount of 0.00002 to 0.2 parts by mass with respect to 100 parts by mass of the compound (A):

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m   (1)

(in Formula (1), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is an (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms; and n and m are each an integer of 1 or 2)

##STR00001##

(in Formula (2), R is (—R.sub.2—(OCO—R.sub.1), and R.sub.1 and R.sub.2 are the same as those in Formula (1)).

A composition is provided including a compound (A) represented by Formula (1) and a compound (B) represented by Formula (2), wherein the compound (B) is contained in an amount of 0.00002 to 0.2 parts by mass with respect to 100 parts by mass of the compound (A):

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m   (1)

(in Formula (1), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is an (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms; and n and m are each an integer of 1 or 2)

##STR00001##

(in Formula (2), R is (—R.sub.2—(OCO—R.sub.1), and R.sub.1 and R.sub.2 are the same as those in Formula (1)).

The invention is related to a composition excellent in stability during storage and excellent stability during utilization, and related to a method of producing the composition. The composition comprises a compound (A) represented by general formula (1) and a compound (B). The compound (B) is an oligomer in which two or more molecules of the compound (A) are bonded to each other by ethylenically unsaturated groups of each compound (A). The composition contains 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)

wherein in general formula (1), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contain an ether group; and n and in each represent an integer of one or two.

The invention is related to a composition excellent in stability during storage and excellent stability during utilization, and related to a method of producing the composition. The composition comprises a compound (A) represented by general formula (1) and a compound (B). The compound (B) is an oligomer in which two or more molecules of the compound (A) are bonded to each other by ethylenically unsaturated groups of each compound (A). The composition contains 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)

wherein in general formula (1), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contain an ether group; and n and in each represent an integer of one or two.